WO2005012355B1 - Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis - Google Patents

Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis

Info

Publication number
WO2005012355B1
WO2005012355B1 PCT/ES2004/070059 ES2004070059W WO2005012355B1 WO 2005012355 B1 WO2005012355 B1 WO 2005012355B1 ES 2004070059 W ES2004070059 W ES 2004070059W WO 2005012355 B1 WO2005012355 B1 WO 2005012355B1
Authority
WO
WIPO (PCT)
Prior art keywords
activity
bioactive
egg white
seq
peptides
Prior art date
Application number
PCT/ES2004/070059
Other languages
Spanish (es)
French (fr)
Other versions
WO2005012355A1 (en
Inventor
Castro Marta Miguel
Fandino Rosina Lopez-Alonso
Sanchez Maria Isidra Recio
Gonzalez Maria Mercedes Ramos
De Artinano Amaya Aleixandre
Original Assignee
Consejo Superior Investigacion
Castro Marta Miguel
Fandino Rosina Lopez-Alonso
Sanchez Maria Isidra Recio
Gonzalez Maria Mercedes Ramos
De Artinano Amaya Aleixandre
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Consejo Superior Investigacion, Castro Marta Miguel, Fandino Rosina Lopez-Alonso, Sanchez Maria Isidra Recio, Gonzalez Maria Mercedes Ramos, De Artinano Amaya Aleixandre filed Critical Consejo Superior Investigacion
Priority to DK04766983T priority Critical patent/DK1661913T3/en
Priority to EP04766983A priority patent/EP1661913B1/en
Priority to JP2006521598A priority patent/JP2007523045A/en
Priority to DE602004012289T priority patent/DE602004012289T2/en
Publication of WO2005012355A1 publication Critical patent/WO2005012355A1/en
Publication of WO2005012355B1 publication Critical patent/WO2005012355B1/en
Priority to US11/343,263 priority patent/US8227207B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/81—Protease inhibitors
    • C07K14/8103—Exopeptidase (E.C. 3.4.11-19) inhibitors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00—Working-up of proteins for foodstuffs
    • A23J3/04—Animal proteins
    • A23J3/08—Dairy proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00—Working-up of proteins for foodstuffs
    • A23J3/30—Working-up of proteins for foodstuffs by hydrolysis
    • A23J3/32—Working-up of proteins for foodstuffs by hydrolysis using chemical agents
    • A23J3/34—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes
    • A23J3/341—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of animal proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/01—Hydrolysed proteins; Derivatives thereof
    • A61K38/012—Hydrolysed proteins; Derivatives thereof from animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/38—Albumins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/465—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from birds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/76—Albumins
    • C07K14/77—Ovalbumin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P21/00—Preparation of peptides or proteins
    • C12P21/06—Preparation of peptides or proteins produced by the hydrolysis of a peptide bond, e.g. hydrolysate products

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nutrition Science (AREA)
  • Biophysics (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Toxicology (AREA)
  • Wood Science & Technology (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

The invention relates to the production of ovoproducts containing bioactive peptides from the egg white subjected to enzymatic treatment. Said peptides have an inhibiting activity of the angiotensin converting enzyme (ACE inhibiting activity) in vitro and/or anti-hypertensive activity in rats and/or antioxidant activity. Said ovoproducts, complete hydrolizates, the fractions thereof with low molecular weight or their constituent peptides could be used as therapeutic substances with ACE inhibiting activity and/or anti-hypertensive activity and/or anti-oxidant activity, either as functional food products, food additives or ingredients or pharmaceutical products for the treatment and/or prevention of hypertension in all its forms in humans or animals and for the treatment and/or prevention of any disorder associated with hypertension in humans or animals.

Claims

26 REIVINDICACIONES MODIFICADAS [recibidas por la oficina Internacional el 26 de enero de 2005 (26.01.05); reivindicación originales de 1-13 reemplazada por las reivindicaciones modificadas de 1-13 (2 páginas)] + Declaración 1. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo caracterizado por a. poseer actividad IECA in vitro y/o actividad antihipertensiva in vivo y/o actividad antioxidante. b. tener un peso molecular comprendido entre 365, 26 MODIFIED CLAIMS [received by the International Office on January 26, 2005 (06.26.05); original claim of 1-13 replaced by modified claims 1-13 (2 pages)] + Statement 1. Bioactive product identified from enzymatic hydrolysis of egg white proteins characterized by a. possess in vitro ACEI activity and / or antihypertensive activity in vivo and / or antioxidant activity. b. have a molecular weight between 365,
2 y 1152,58 c. ser péptido identificado con las secuencias de aminoácidos del grupo siguiente: SEQ. ID. N°. 1, SEQ. ID. N°. 3, SEQ. LD. N°. 4, SEQ. LO. N°. 6, SEQ. ID. N°. 7 y SEQ. ID. N°. 8 2. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo según la reivindicación 1 caracterizado por obtenerse mediante un procedimiento de síntesis química o enzimática o mediante métodos recombinantes. 2 and 1152.58 c. to be a peptide identified with the amino acid sequences of the following group: SEQ. ID. N °. 1, SEQ. ID. N °. 3, SEQ. LD. N °. 4, SEQ. THE. N °. 6, SEQ. ID. N °. 7 and SEQ. ID. N °. 2. Bioactive product identified from enzymatic hydrolysis of egg white proteins according to claim 1, characterized by being obtained by a chemical or enzymatic synthesis process or by recombinant methods.
3. Procedimiento para producir cualquiera de los productos bioactivos según la reivindicación 1 y 2 y el péptido de SEQ ID N°2,. caracterizado por a. obtenerse por hidrólisis del material de partida que sería cualquier sustrato apropiado que contenga una o más proteínas o péptidos, de origen animal, vegetal o procedentes de microoganismos, preferiblemente ovoalbúmina o clara de huevo que cuya secuencia de aminoácidos comprendiese la secuencia de aminoácidos de alguno de los péptidos bioactivos de interés indicados en la reivindicación 1 o y el péptido de SEQ ID N°2. b. disolverse o dispersarse dicho material de partida, a una concentración apropiada, en agua o en una disolución tampón, a un pH adecuado para la actuación de la enzima proteolítica, c. emplearse cualquier enzima proteolítica capaz de romper la proteína presente en el material de partida y proporcionar los péptidos de interés, pero preferiblemente pepsina a pH 2-0-3.0; o microorganismos proteolíticos que llevaran a cabo una fermentación del sustrato, y d. el tiempo de reacción estaría comprendido entre 10 min y 24 horas, pero, preferiblemente durante un tiempo inferior a 3 horas. 3. Process for producing any of the bioactive products according to claim 1 and 2 and the peptide of SEQ ID No. 2 ,. characterized by a. obtained by hydrolysis of the starting material which would be any appropriate substrate containing one or more proteins or peptides, of animal, vegetable or micro-organism origin, preferably ovalbumin or egg white whose amino acid sequence comprised the amino acid sequence of the bioactive peptides of interest indicated in claim 1 and the peptide of SEQ ID No. 2. b. dissolving or dispersing said starting material, at an appropriate concentration, in water or in a buffer solution, at a pH suitable for the actuation of the proteolytic enzyme, c. any proteolytic enzyme capable of breaking the protein present in the starting material and providing the peptides of interest, but preferably pepsin at pH 2-0-3.0; or proteolytic microorganisms that will carry out a fermentation of the substrate, and d. the reaction time would be between 10 min and 24 hours, but preferably for a time of less than 3 hours.
4. Procedimiento para producir productos bioactivos según la reivindicación 3 caracterizado por emplear altas presiones hidrostáticas entre 100 y 1000 MPa, preferentemente 400 MPa, para acelerar la hidrólisis del sustrato sin inhibir la enzima proteolítica y/o modificar el perfil de los péptidos obtenidos Process for producing bioactive products according to claim 3 characterized by using high hydrostatic pressures between 100 and 1000 MPa, preferably 400 MPa, to accelerate the hydrolysis of the substrate without inhibiting the proteolytic enzyme and / or modifying the profile of the peptides obtained
5. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo caracterizado porque para su obtención se emplean los procedimientos indicados en la reivindicaciones 3 y 4,5. Bioactive product identified from enzymatic hydrolysis of egg white proteins characterized in that the procedures indicated in claims 3 and 4 are used to obtain them;
6. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo según la reivindicación 5 caracterizado porque el material de partida es entre otros, ovoalbúmina pura, clara de huevo y huevo entero en sus diferentes formas de presentación, u ovoproductos destinados a hostelería y restauración, complementos dietéticos para deportistas o~voproductos para alimentación animal.6. Bioactive product identified from enzymatic hydrolysis of egg white proteins according to claim 5, characterized in that the starting material is, among others, pure ovalbumin, egg white and whole egg in its different forms of presentation, or egg products intended hospitality and catering, dietary supplements for athletes or ~ voproductos for animal feed.
7. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo según la reivindicación 6 caracterizado porque se trata del hidrolizado enzimático, cualquiera de sus fracciones, o una purificación de los mismos que contenga al menos alguno de los péptidos indicados en la reivindicación 17. Bioactive product identified from enzymatic hydrolysis of egg white proteins according to claim 6, characterized in that it is the enzymatic hydrolyzate, any of its fractions, or a purification thereof containing at least some of the peptides indicated in claim 1
8. Producto bioactivo identificado a partir de hidrólisis enzimática de proteínas de la clara de huevo caracterizados por ser derivados o sales farmacéuticamente aceptables o sus mezclas de cualquiera de los productos bioactivos indicados en las reivindicaciones 1, 2, 5,6 y 7.8. Bioactive product identified from enzymatic hydrolysis of egg white proteins characterized by being derivatives or pharmaceutically acceptable salts or their mixtures of any of the bioactive products indicated in claims 1, 2, 5, 6 and 7.
9. Composición farmacéutica caracterizada por comprender al menos alguno de los productos bioactivos con actividad 3ECA in vitro y/o actividad antihipertensiva in vivo y/o actividad antioxidante según las reivindicaciones 1, 2, 5, 6 y 7. Pharmaceutical composition characterized by comprising at least some of the bioactive products with 3ECA activity in vitro and / or antihypertensive activity in vivo and / or antioxidant activity according to claims 1, 2, 5, 6 and 7.
10. Aditivo, ingrediente o suplemento alimentario funcional caracterizada por comprender al menos alguno de los productos bioactivos con actividad IECA in vitro y/o actividad antihipertensiva in vivo y/o actividad antioxidante según las reivindicaciones 1, 2, 5, 6 y 7.10. Additive, ingredient or functional food supplement characterized by comprising at least some of the bioactive products with in vitro ACEI activity and / or antihypertensive activity in vivo and / or antioxidant activity according to claims 1, 2, 5, 6 and 7.
11. Producto alimentario funcional caracterizada por comprender al menos alguno de los productos bioactivos con actividad IECA in vitro y/o actividad antihipertensiva in vivo y/o actividad antioxidante según las reivindicaciones 1, 2, 5,6 y 7.11. Functional food product characterized by comprising at least some of the bioactive products with in vitro ACEI activity and / or antihypertensive activity in vivo and / or antioxidant activity according to claims 1, 2, 5, 6 and 7.
12. Uso de la composición farmacéutica según la reivindicación 9 en la elaboración de un medicamento para el tratamiento de la hipertensión. 12. Use of the pharmaceutical composition according to claim 9 in the preparation of a medicament for the treatment of hypertension.
13. Uso de aditivo, ingrediente, alimentario funcional según la reivindicación 9 en la elaboración de un producto alimentario funcional favorable para reducir la hipertensión. 13. Use of additive, ingredient, functional food according to claim 9 in the production of a favorable functional food product to reduce hypertension.
PCT/ES2004/070059 2003-07-31 2004-07-23 Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis WO2005012355A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DK04766983T DK1661913T3 (en) 2003-07-31 2004-07-23 Bioactive peptides derived from egg white protein through enzymatic hydrolysis
EP04766983A EP1661913B1 (en) 2003-07-31 2004-07-23 Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis
JP2006521598A JP2007523045A (en) 2003-07-31 2004-07-23 Bioactive peptide derived from egg white protein by enzymatic hydrolysis
DE602004012289T DE602004012289T2 (en) 2003-07-31 2004-07-23 BIOACTIVE PEPTIDES OBTAINED BY ENZYMATIC HYDROLYSIS FROM THE PROTEINS OF EGG WHITE
US11/343,263 US8227207B2 (en) 2003-07-31 2006-01-30 Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200301829A ES2253036B1 (en) 2003-07-31 2003-07-31 BIOACTIVE PEPTIDES DERIVED FROM PROTEINS OF THE EGG CLEAR BY ENZYMATIC HYDROLYSIS.
ESP200301829 2003-07-31

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/343,263 Continuation US8227207B2 (en) 2003-07-31 2006-01-30 Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis

Publications (2)

Publication Number Publication Date
WO2005012355A1 WO2005012355A1 (en) 2005-02-10
WO2005012355B1 true WO2005012355B1 (en) 2005-03-24

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PCT/ES2004/070059 WO2005012355A1 (en) 2003-07-31 2004-07-23 Bioactive peptides derived from the proteins of egg white by means of enzymatic hydrolysis

Country Status (8)

Country Link
US (1) US8227207B2 (en)
EP (1) EP1661913B1 (en)
JP (1) JP2007523045A (en)
AT (1) ATE388166T1 (en)
DE (1) DE602004012289T2 (en)
DK (1) DK1661913T3 (en)
ES (2) ES2253036B1 (en)
WO (1) WO2005012355A1 (en)

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ES2329316B1 (en) * 2005-05-23 2010-10-14 Consejo Superior Investig. Cientificas OBTAINING AND ANTIHIPERTENSIVE PROPERTIES OF PEPTIDES DERIVED FROM EGG CLEAR PROTEINS.
JP2008156344A (en) * 2006-11-27 2008-07-10 Q P Corp In vivo antioxidant, food composition for in vivo antioxidation, pharmaceutical composition for in vivo antioxidation, and inhibitor for liver function disturbance, food composition for inhibition of liver function disturbance and pharmaceutical composition for inhibition of liver function disturbance
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CA2793800A1 (en) * 2009-03-20 2010-09-23 The Governors Of The University Of Alberta Peptides that inhibit angiotensin converting enzyme and peptides with antioxidant activity purified from ovotransferrin and methods of producing and using the same
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WO2015082741A1 (en) * 2013-12-04 2015-06-11 Consejo Superior De Investigaciones Cientificas (Csic) Use of multifunctional bioactive products derived from the enzymatic hydrolysis of egg white proteins for treating metabolic syndrome
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KR102056348B1 (en) 2018-05-28 2019-12-16 주식회사 바이오프로후즈 Manufacturing method of egg white protein hydrolysate and use thereof
CN109485696B (en) * 2018-11-06 2020-10-23 渤海大学 Membrane peptidase inhibitory peptide for overcoming intestinal degradation
MX2022000374A (en) 2019-07-11 2022-03-25 Clara Foods Co Protein compositions and consumable products thereof.
US10927360B1 (en) 2019-08-07 2021-02-23 Clara Foods Co. Compositions comprising digestive enzymes
CN110628856A (en) * 2019-10-17 2019-12-31 武汉普诺金生物科技股份有限公司 Antihypertensive small molecular peptide, and preparation method and application thereof
CN112616925A (en) * 2020-12-30 2021-04-09 光明乳业股份有限公司 Double-protein fermented milk and preparation method thereof
EP4046649A1 (en) 2021-02-22 2022-08-24 Bioseutica B.V. Ovotransferrins for use in the treatment of iron deficiency anaemia
CN117264018B (en) * 2023-09-26 2024-04-09 南京工业大学 Preparation and application of functional peptide in pigeon egg white

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Also Published As

Publication number Publication date
DE602004012289T2 (en) 2009-09-03
ES2253036B1 (en) 2007-07-16
EP1661913A1 (en) 2006-05-31
US20060280804A1 (en) 2006-12-14
US8227207B2 (en) 2012-07-24
DE602004012289D1 (en) 2008-04-17
ES2303090T3 (en) 2008-08-01
WO2005012355A1 (en) 2005-02-10
JP2007523045A (en) 2007-08-16
ATE388166T1 (en) 2008-03-15
DK1661913T3 (en) 2008-07-07
ES2253036A1 (en) 2006-05-16
EP1661913B1 (en) 2008-03-05

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